PL201810B1 - Sposób syntezy N-[(1S,2R)-3-(4-amino-N-izobutylobenzenosulfonoamido)-1-benzylo-2-hydroksypropylo]-karbaminianu (3S)-tetrahydro-3-furylu - Google Patents
Sposób syntezy N-[(1S,2R)-3-(4-amino-N-izobutylobenzenosulfonoamido)-1-benzylo-2-hydroksypropylo]-karbaminianu (3S)-tetrahydro-3-furyluInfo
- Publication number
- PL201810B1 PL201810B1 PL342602A PL34260299A PL201810B1 PL 201810 B1 PL201810 B1 PL 201810B1 PL 342602 A PL342602 A PL 342602A PL 34260299 A PL34260299 A PL 34260299A PL 201810 B1 PL201810 B1 PL 201810B1
- Authority
- PL
- Poland
- Prior art keywords
- compound
- formula
- product
- reacting
- carried out
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 108010010369 HIV Protease Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 230000008569 process Effects 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- -1 p-nitrophenylsulfonyl halide Chemical class 0.000 claims description 29
- 239000000047 product Substances 0.000 claims description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 8
- XDPCNPCKDGQBAN-BYPYZUCNSA-N (3s)-oxolan-3-ol Chemical compound O[C@H]1CCOC1 XDPCNPCKDGQBAN-BYPYZUCNSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- BPSUJSDZHLTNJR-UHFFFAOYSA-N sulfamide;hydrochloride Chemical compound Cl.NS(N)(=O)=O BPSUJSDZHLTNJR-UHFFFAOYSA-N 0.000 description 4
- JNODDICFTDYODH-UHFFFAOYSA-N 2-hydroxytetrahydrofuran Chemical group OC1CCCO1 JNODDICFTDYODH-UHFFFAOYSA-N 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- AUYHZFAGBOOPMD-CMXBXVFLSA-N n-[(2r,3s)-3-amino-2-hydroxy-4-phenylbutyl]-n-(2-methylpropyl)-4-nitrobenzenesulfonamide;hydrochloride Chemical compound Cl.C([C@H](N)[C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(=CC=1)[N+]([O-])=O)C1=CC=CC=C1 AUYHZFAGBOOPMD-CMXBXVFLSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NVEPLQDORJSXRO-DLBZAZTESA-N tert-butyl n-[(2s,3r)-3-hydroxy-4-(2-methylpropylamino)-1-phenylbutan-2-yl]carbamate Chemical compound CC(C)CNC[C@@H](O)[C@@H](NC(=O)OC(C)(C)C)CC1=CC=CC=C1 NVEPLQDORJSXRO-DLBZAZTESA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- IUFITGQVUSROFE-QMMMGPOBSA-N [(2s)-2-imidazol-1-yloxolan-2-yl] carbamate Chemical compound C1=CN=CN1[C@@]1(OC(=O)N)CCCO1 IUFITGQVUSROFE-QMMMGPOBSA-N 0.000 description 1
- GDHPHPNSFSAFPD-ZETCQYMHSA-N [(3s)-oxolan-3-yl] imidazole-1-carboxylate Chemical compound C1=CN=CN1C(=O)O[C@H]1CCOC1 GDHPHPNSFSAFPD-ZETCQYMHSA-N 0.000 description 1
- 125000006242 amine protecting group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9805898.5A GB9805898D0 (en) | 1998-03-20 | 1998-03-20 | Process for the sythesis of hiv protease inhibitors |
| PCT/GB1999/000852 WO1999048885A1 (en) | 1998-03-20 | 1999-03-18 | Process for the synthesis of hiv protease inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL342602A1 PL342602A1 (en) | 2001-06-18 |
| PL201810B1 true PL201810B1 (pl) | 2009-05-29 |
Family
ID=10828884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL342602A PL201810B1 (pl) | 1998-03-20 | 1999-03-18 | Sposób syntezy N-[(1S,2R)-3-(4-amino-N-izobutylobenzenosulfonoamido)-1-benzylo-2-hydroksypropylo]-karbaminianu (3S)-tetrahydro-3-furylu |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6281367B1 (cs) |
| EP (1) | EP1066276B1 (cs) |
| JP (1) | JP3363439B2 (cs) |
| KR (1) | KR100555278B1 (cs) |
| CN (1) | CN1308319C (cs) |
| AP (1) | AP1226A (cs) |
| AT (1) | ATE242772T1 (cs) |
| AU (1) | AU751534B2 (cs) |
| BR (1) | BR9908970A (cs) |
| CA (1) | CA2324217C (cs) |
| CZ (1) | CZ299193B6 (cs) |
| DE (1) | DE69908761T2 (cs) |
| DK (1) | DK1066276T3 (cs) |
| EA (1) | EA003022B1 (cs) |
| EE (1) | EE04750B1 (cs) |
| ES (1) | ES2203090T3 (cs) |
| GB (1) | GB9805898D0 (cs) |
| HK (1) | HK1032047A1 (cs) |
| HR (1) | HRP20000609B1 (cs) |
| HU (1) | HUP0105439A3 (cs) |
| ID (1) | ID26587A (cs) |
| IL (1) | IL138127A (cs) |
| IS (1) | IS2273B (cs) |
| NO (1) | NO317648B1 (cs) |
| NZ (1) | NZ506563A (cs) |
| PL (1) | PL201810B1 (cs) |
| PT (1) | PT1066276E (cs) |
| RS (1) | RS49954B (cs) |
| SK (1) | SK283939B6 (cs) |
| TR (1) | TR200002698T2 (cs) |
| WO (1) | WO1999048885A1 (cs) |
| ZA (1) | ZA200004482B (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5843946A (en) | 1992-08-25 | 1998-12-01 | G.D. Searle & Co. | α-and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
| US6548706B2 (en) * | 1999-12-23 | 2003-04-15 | Aerojet Fine Chemicals Llc | Preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl) -p-nitrobenzenesulfonylamide hydrochloride and other derivatives of 2-hydroxy-1,3-diamines |
| EP2314564A3 (en) * | 1999-12-23 | 2012-04-04 | Ampac Fine Chemicals LLC | Improved preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride and other derivatives of 2-hydroxy-1,3-diamines |
| HUE034389T2 (en) | 2002-05-16 | 2018-02-28 | Janssen Sciences Ireland Uc | Pseudopolymorphic forms of an HIV protease inhibitor |
| US7772411B2 (en) | 2003-12-23 | 2010-08-10 | Tibotec Pharmaceuticals Ltd. | Process for the preparation of (3R,3aS,6aR)-hexahydrofuro [2,3-b] furan-3-yl (1S,2R)-3[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate |
| AR073248A1 (es) | 2008-09-01 | 2010-10-20 | Tibotec Pharm Ltd | Proceso para la preparacion de (1s, 2r)-3- ((4-aminofenil) sulfonil) ( isobutil) amino)-1- bencil-2- hidroxipropilcarbamato de (3r, 3as,6ar)- hexahidrofuro-(2,3-b) furan-3- ilo (darunavir) y compuestos intermediarios utiles en dicho proceso. |
| AP3551A (en) | 2010-01-27 | 2016-01-18 | Viiv Healthcare Co | Antiviral therapy |
| WO2012032389A2 (en) | 2010-09-10 | 2012-03-15 | Lupin Limited | Process for preparation of substantially pure fosamprenavir calcium and its intermediates |
| CN111233794A (zh) * | 2020-03-27 | 2020-06-05 | 江巨东 | 一种安普那韦的精制方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1071930A (zh) * | 1991-07-10 | 1993-05-12 | 伊莱利利公司 | 用作治疗艾滋病的人免疫缺陷病毒蛋白酶的抑制剂 |
| US5843946A (en) * | 1992-08-25 | 1998-12-01 | G.D. Searle & Co. | α-and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
| US5723490A (en) * | 1992-09-08 | 1998-03-03 | Vertex Pharmaceuticals Incorporated | THF-containing sulfonamide inhibitors of aspartyl protease |
| IS2334B (is) * | 1992-09-08 | 2008-02-15 | Vertex Pharmaceuticals Inc., (A Massachusetts Corporation) | Aspartyl próteasi hemjari af nýjum flokki súlfonamíða |
-
1998
- 1998-03-20 GB GBGB9805898.5A patent/GB9805898D0/en not_active Ceased
-
1999
- 1999-03-18 AT AT99910543T patent/ATE242772T1/de not_active IP Right Cessation
- 1999-03-18 CA CA002324217A patent/CA2324217C/en not_active Expired - Fee Related
- 1999-03-18 US US09/646,277 patent/US6281367B1/en not_active Expired - Lifetime
- 1999-03-18 SK SK1373-2000A patent/SK283939B6/sk not_active IP Right Cessation
- 1999-03-18 IL IL13812799A patent/IL138127A/xx not_active IP Right Cessation
- 1999-03-18 ES ES99910543T patent/ES2203090T3/es not_active Expired - Lifetime
- 1999-03-18 TR TR2000/02698T patent/TR200002698T2/xx unknown
- 1999-03-18 AU AU29475/99A patent/AU751534B2/en not_active Ceased
- 1999-03-18 CN CNB998042242A patent/CN1308319C/zh not_active Expired - Fee Related
- 1999-03-18 KR KR1020007010359A patent/KR100555278B1/ko not_active IP Right Cessation
- 1999-03-18 EA EA200000859A patent/EA003022B1/ru unknown
- 1999-03-18 AP APAP/P/2000/001911A patent/AP1226A/en active
- 1999-03-18 DK DK99910543T patent/DK1066276T3/da active
- 1999-03-18 CZ CZ20003457A patent/CZ299193B6/cs not_active IP Right Cessation
- 1999-03-18 NZ NZ506563A patent/NZ506563A/en unknown
- 1999-03-18 JP JP2000537868A patent/JP3363439B2/ja not_active Expired - Lifetime
- 1999-03-18 PT PT99910543T patent/PT1066276E/pt unknown
- 1999-03-18 PL PL342602A patent/PL201810B1/pl not_active IP Right Cessation
- 1999-03-18 BR BR9908970-0A patent/BR9908970A/pt not_active Application Discontinuation
- 1999-03-18 EE EEP200000568A patent/EE04750B1/xx not_active IP Right Cessation
- 1999-03-18 RS YUP-559/00A patent/RS49954B/sr unknown
- 1999-03-18 WO PCT/GB1999/000852 patent/WO1999048885A1/en active IP Right Grant
- 1999-03-18 HU HU0105439A patent/HUP0105439A3/hu unknown
- 1999-03-18 ID IDW20001857A patent/ID26587A/id unknown
- 1999-03-18 EP EP99910543A patent/EP1066276B1/en not_active Expired - Lifetime
- 1999-03-18 DE DE69908761T patent/DE69908761T2/de not_active Expired - Lifetime
-
2000
- 2000-08-29 IS IS5605A patent/IS2273B/is unknown
- 2000-08-29 ZA ZA200004482A patent/ZA200004482B/en unknown
- 2000-09-15 HR HR20000609A patent/HRP20000609B1/xx not_active IP Right Cessation
- 2000-09-19 NO NO20004664A patent/NO317648B1/no not_active IP Right Cessation
-
2001
- 2001-03-30 HK HK01102333A patent/HK1032047A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20060126965A (ko) | 활성 아민기 존재하에서 ｏ-카바모일 화합물을 제조하는방법 | |
| PL201810B1 (pl) | Sposób syntezy N-[(1S,2R)-3-(4-amino-N-izobutylobenzenosulfonoamido)-1-benzylo-2-hydroksypropylo]-karbaminianu (3S)-tetrahydro-3-furylu | |
| JP6454707B2 (ja) | ｔｒａｎｓ−８−クロロ−５−メチル−１−［４−（ピリジン−２−イルオキシ）−シクロヘキシル］−５，６−ジヒドロ−４Ｈ−２，３，５，１０ｂ−テトラアザ−ベンゾ［ｅ］アズレン及びその結晶形態の合成 | |
| JP7379384B2 (ja) | リフィテグラストの製造方法 | |
| US5534637A (en) | Starting materials for prepartion of sulfonylurea derivatives and process for preparing the same | |
| MXPA00008925A (en) | Process for the synthesis of hiv protease inhibitors | |
| JPH11349567A (ja) | ３―アミノ―２―オキソ―ピロリジンの製造方法、新規中間体およびその使用 | |
| RU2761167C1 (ru) | Способ получения картолина-2 | |
| RU2775690C2 (ru) | Синтез транс-8-хлор-5-метил-1-[4-(пиридин-2-илокси)-циклогексил]-5,6-дигидро-4н-2,3,5,10в-тетраазабензо[e]азулена и его кристаллические формы | |
| KR102441327B1 (ko) | 다이아미노피리미딘 유도체 또는 이의 산부가염의 신규의 제조방법 | |
| JP4176163B2 (ja) | １−｛［２−（シクロプロピルカルボニル）フエニル］スルフアモイル｝−３−（４，６−ジアルコキシ−２−ピリミジニル）尿素化合物の製造方法及びその製造のための中間体 | |
| US6063962A (en) | Process for the preparation of NMDA antagonists | |
| RU2051903C1 (ru) | Способ получения (*01+)-(е)-4-этил-2-[(е)-гидроксиимино]-5-нитро-3-гексенамида | |
| JPH0525111A (ja) | 脂肪族アミドまたはその塩の製法 | |
| JPH0211562A (ja) | ４―メチル―３―チオセミカルバジドの製造法 | |
| JPH09110819A (ja) | Ｎ−（４−ブロモ−２− フルオロベンジル） カルバメートおよびその製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| VDSO | Invalidation of derivated patent or utility model |
Ref document number: 386060 Country of ref document: PL |
|
| VDSO | Invalidation of derivated patent or utility model |
Ref document number: 386060 Country of ref document: PL |